HCID 54001178, compound → HCID 10158981, compound

HRID 2305304Notes

Reaction equation

HRID 2305304 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10](=[O:22])[C:11]3[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]([OH:21])=[O:20])=[CH:13][CH:12]=3)=[C:8]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[S:7][C:6]=2[CH:30]=1>CCO.CCOC(C)=O.[Pd]>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10](=[O:22])[C:11]3[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:15][CH:16]=3)=[C:8]([C:23]3[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=3)[S:7][C:6]=2[CH:30]=1

Participants

5

Reactant 1

HCID 54001178HCID 54001178, compound

Product 1

HCID 10158981HCID 10158981, compoundYield 72.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-hydroxy-3-[4-(2-carboxyvinyl)benzoyl]-2-(4-hydroxyphenyl)benzo[b]thiophene (310 mg, 0.74 mmol) was dissolved in 50 mL of a 1:1 mixture of EtOH and EtOAc. This solution was hydrogenated at 40 psi in the presence of 10% Pd/C (200 mg). When the reaction was judged complete by TLC analysis, the mixture was filtered through Celite to remove the catalyst. The filtrated was concentrated in vacuo to a yellow oil that was triturated from hexanes/EtOAc. Filtration provided 225 mg (72%) of 6-hydroxy-3-[4-(2-carboxyethyl)benzoyl]-2-(4-hydroxyphenyl)benzo[b]thiophene as a yellow solid. mp 244-248° C. 1H NMR (DMSO-d6) δ 12.15 (bs, 1H), 9.74 (S, 1H), 9.68 (S, 1H), 7.56 (d, J=8.1 Hz, 2H), 7.30 (d, J=2.0 Hz, 1 H), 7.23-7.19 (m, 3H), 7.12 (d, J=8.5 Hz, 2H), 6.82 (dd, J=9.0, 2.0 Hz, 1H), 6.62 (d, J=8.5 Hz, 2H), 2.77 (t, J=7.0 Hz, 2H), 2.45 (t, J=7.0 Hz, 2). FD mass spec: 418. Anal. Calcd. for C24H18O5S.20 H2O: C, 68.89; H, 4.34. Found: C, 68.35; H, 4.72.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. customto remove the catalyst
  3. concentrationThe filtrated was concentrated in vacuo to a yellow oil that
  4. customwas triturated from hexanes/EtOAc
  5. filtrationFiltration

Sources & evidence

ORD record
ord-0d58c2a143db46c6b19847ff56761e77
Source dataset
uspto-grants-2002_08
Patent number
US06440958B1

Reaction notes

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